One of the industrial processes for the preparation of phenol, discussed in Section 24.6, includes an acid-catalyzed

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One of the industrial processes for the preparation of phenol, discussed in Section 24.6, includes an acid-catalyzed rearrangement of cumene hydroperoxide as a key step. This reaction proceeds by way of an intermediate hemiacetal:
One of the industrial processes for the preparation of phenol,

You learned in Section 17.8 of the relationship among hemiacetals, ketones, and alcohols; the formation of phenol and acetone is simply an example of hemiacetal hydrolysis. The formation of the hemiacetal intermediate is a key step in the synthetic procedure; it is the step in which the aryl-oxygen bond is generated. Can you suggest a reasonable mechanism for this step?

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Organic Chemistry

ISBN: 978-0072905014

4th edition

Authors: Francis A. Carey

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